Calcium Chloride → HCID 69217707, compound

HRID 2222041Notes

Reaction equation

HRID 2222041 reaction equation
[CH2:1]([C:3]1[S:4][CH:5]=[C:6](/[CH:8]=[CH:9]/[C:10]2[C:11]([O:21][CH2:22][C:23]3[CH:45]=[CH:44][C:26]([O:27][CH2:28][C:29]4[N:30]=[C:31]([C:35]5[CH:40]=[CH:39][CH:38]=[C:37]([N+:41]([O-])=O)[CH:36]=5)[O:32][C:33]=4[CH3:34])=[C:25]([O:46][CH3:47])[CH:24]=3)=[N:12][N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:14]=2)[N:7]=1)[CH3:2].[Cl-].[Ca+2].[Cl-]>[Fe].C(O)C>[CH2:1]([C:3]1[S:4][CH:5]=[C:6](/[CH:8]=[CH:9]/[C:10]2[C:11]([O:21][CH2:22][C:23]3[CH:45]=[CH:44][C:26]([O:27][CH2:28][C:29]4[N:30]=[C:31]([C:35]5[CH:36]=[C:37]([NH2:41])[CH:38]=[CH:39][CH:40]=5)[O:32][C:33]=4[CH3:34])=[C:25]([O:46][CH3:47])[CH:24]=3)=[N:12][N:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:14]=2)[N:7]=1)[CH3:2]

Participants

5

Reactant 2

HCID 5284359Calcium ChlorideHCID 69216429HCID 69216429, compound

Product 1

HCID 69217707HCID 69217707, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of {4-({4-[({4-[(E)-2-(2-ethyl-1,3-thiazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-2-(3-nitrophenyl)-1,3-oxazole (650 mg), iron (reduced) (284 mg), calcium chloride (11 mg) and 80% ethanol (8 mL) was heated under reflux for 2 hrs. Insoluble materials were removed by celite filtration, and the filtrate was concentrated. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate to give {3-[4-({4-[({4-[(E)-2-(2-ethyl-1,3-thiazol-4-yl)ethenyl]-1-phenyl-1H-pyrazol-3-yl}oxy)methyl]-2-methoxyphenoxy}methyl)-5-methyl-1,3-oxazol-2-yl]phenyl}amine as yellow amorphous form (150 mg, yield 38%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hrs
  3. customInsoluble materials were removed by celite filtration
  4. concentrationthe filtrate was concentrated
  5. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-11df439b65d9479dafdd93c6725c0081
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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